What I Learned at Startup Weekend: 12 Lessons on Leaping, Connecting, and Finishing

Startup Weekend is a singular experience. It’s not for the faint of heart, but the magic is that the simple act of attending a Startup Weekend unfaintens you. Only by doing something like this do you discover that your heart is as strong as you want it to be.

Startup Weekend throws you together in a room with dozens of other people, many of whom you haven’t met. Anyone who wants to can pitch an idea for a company. Everyone votes for their favorite ideas, the best ones are selected, and the winning ideas become teams. You work for 54 hours trying to make the company real. You get out and talk to people you think have the problem you’re trying to solve, and if they do, you build whatever the hell you can before the bell rings. At the end the teams pitch again, and a table of judges selects the winners.

But it’s not about winning. (And I’m not just saying that because my team didn’t win.) It’s about learning.

1. You advance the fastest by making things happen.

This is the single most important thing to learn about being an entrepreneur. You can, and should, read all the Lean Startup books you can get your hands on. But it’s not enough.  This knowledge is fragile. And if you don’t test it in the real world, you never find out which of it is going to break. Every situation is unique and there is no gospel. The ugly truth is that you can read and read and read, but you will still never know what you’re doing, at first. Maybe you never really know. Reading books is great, but it also lulls you into a feeling of security in your knowledge. Learning and doing is not an either-or decision. It’s both-and.

2. You must get out into the real world.

The reason learning-by-doing is so important is because it forces you into the real world. And in the real world, there are people. People are the world. The overriding lesson of Startup Weekend is that your idea means nothing if you can’t validate it with real people. This is a much-discussed but, I believe, still little-understood principle, for those who haven’t experienced it. Our Startup Weekend champion was a company called Baby Steps. Their idea wasn’t the most impressive or inventive, but it was the best. Why? They understood their customer and they proved that their customer wanted what they had to offer. Other teams had slick websites and fancy app prototypes. Baby Steps knew who they could help and how they would do it.

3. Talking to people is hard as hell.

Which is probably why most people don’t do it. Getting rejected really sucks. Whether it’s someone who doesn’t want to talk to you at all, or someone who doesn’t understand the problem or belittles it, or someone who couldn’t care less about your idea, or someone who takes offense at something you say: it’s all viscerally painful. So what separates those who try it and persist at it, from those who never try it, and those who try it and give up? I don’t know. I’m not there yet, but I’m going to learn. My hunch? If you just keep doing it, you realize that while it’s always painful to get rejected, each time you do, it’s a tiny bit less painful than the last time. You get familiar with the feeling of being rejected. You start becoming friends with it. You start to revel in it, like a pig in mud; you use it as a springboard, you let it bring you to life. Because it makes you stronger.

4. Connecting with other people is an art.

Interviewing users is an art. So is working with a team. So is getting funded. Here’s how I, an introverted quasi-homebody, learned how to relish making new connections. I believe every pair of people in the world has a shared link. A tie that binds. You have the same favorite beer. You both just moved to the same city. You have a mutual friend (or enemy). And you, meeting a new person, are a detective: the game is to figure out what binds the two of you together. To win the game, you must find the tie and cultivate it. Let it bloom. Celebrate it: your tie is unique in the entire world. No other pair of people have exactly the same one.

5. Everyone has something to offer.

The secret of teams is that complementary skills allow each member to go all-out on the one thing they do best, which means they get done faster and produce better work than any single person could. Nine women can’t make a baby in one month, but nine women can make nine babies in nine months, and all those babies can have full sets of hand-sewn clothing from Mother #1, and a room full of furniture constructed by Mother #2, and an array of baby toys constructed by Mother #3 (and so on). And if you dismiss someone for not being good enough, that means you’re the one who’s not good enough at finding what that person’s best skill is and setting them to work.

6. Accountability is king.

After a disappointing user interview, I felt discouraged. I questioned my skills, my purpose, and myself. But I knew I had to put those feelings aside for the time being, because my teammates needed my full efforts. Even if I was down on myself, I wasn’t down on them. And if you can’t do something for yourself, you can always do it for someone else instead. (Check out the short book The Accountability Effect to learn more about this magic.)

7. You get to practice sublimating your ego.

Make it your #1 priority. Try to accept blame for everything. Refuse to take credit for anything. Force yourself to shut your mouth and listen: to your teammates, to the coaches, to the people you’re interviewing. When they stop talking, and you must open your mouth, ask a question. Delight in encouraging others to tell you what they see and what they believe. You can listen to yourself talk any day of the week (and a thousand times on Sundays). P.S.: it’s fucking difficult. That’s why you’re practicing.

8. Own the work but not the outcome.

Should you try to win competitions? Hell yes. Always. Do everything you possibly can. And then, right before the winner is announced, divorce yourself. This is not a verdict. Win or lose, the work is yours, and nobody can take it away. The most important thing? What you’re going to do next.

9. You are not the first one to do this.

Whatever you’re doing, someone has come before you. On Saturday afternoon, we’d just done our user interviews. We were working on formulating some models of our ideal customer. We wanted some feedback, so when we saw one of the coaches walking by, we called him over. He told us, in so many words, “Fuck that. You need to start building your solution. Something. Anything. You’re running out of time.” Bless his heart, he snapped us out of it right before we walked off the precipice. And it had totally been my doing! Maybe because I was scared of trying to execute, or for some other reason, I had been leading us into analysis paralysis purgatory. But I somehow had enough sense to suck it up, put my ego aside, ask for someone’s opinion who knew more than me, and to do what he said. So simple; so hard.

10. You don’t get a gold star for working hard.

It’s part of the deal—a minimum requirement, only. One of the example slides for our final pitch asked us to mention some challenges we faced. I put down that our choice to do a Wizard of Oz prototype (where things look automated to the user, but really you’re doing everything manually) was a challenge, since it meant we had to work for four hours straight manually copying data between the web, email, a spreadsheet, and a browser-based texting app. When our coach saw that slide, he told us to scrap it immediately. “You think people are going to care that you had to do a bunch of work? It’s hard enough to find customers and give them something they want. But now you’re saying it’s also hard to send out a few text messages? Do you want some magical button to do this for you?” Real shit.

11. Nothing is about you.

Your idea? Doesn’t mean shit. It’s about what you can do to help people who have problems and needs. Your pitch? Meaningless, if you don’t demonstrate how what you’re talking about will provide value to the judges or investors or potential employees you’re talking to. This is why you must fully embrace the practice of ego-banishment. Because of course all of these things are important to you. And that’s great. It’s essential. Your ambition and your desire to be great is what makes you you, and it’s what makes you put yourself on the line and stretch your comfort zone. But the sooner you can completely forget about all of that and start making other people look good, the sooner you will understand how to satisfy that ambition and desire, and achieve the things you want.

12. Everything is better when you commit yourself 100%.

I pitched an idea, one I’ve been working on for a long time and thinking about for longer. It fell one vote short of being selected to get worked during the weekend. I could have shut down and left, or joined another team and pouted and half-assed everything I did. Instead, I let it go, I picked a team that I felt passionate about, and I had one of the best weekends of my life. I forged a real connection with someone else, working on a real business, trying to solve real problems for real people. Being committed puts you in rarefied air. So many people, millions of them, who have this kind of opportunity, never commit to anything on this level their whole lives. You don’t have to be smart. You don’t have to be educated. You don’t have to be rich. You just have to care. Care more. Make things happen.